Caribbean Villa Rentals


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Southern Breeze

United States Virgin Islands, St. John

from $629 /night
up to 8 guests

Southern Breeze

4 bedroom 4 bath USVI villa in St. John

Southern Breeze sits high above St. John’s south shore and commands a captivating view of sapphire and emerald bays, the open Caribbean, and verdant mountains.

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Symbio

British Virgin Islands, Virgin Gorda

from $619 /night
up to 4 guests

Symbio

3 bedroom 4 bath BVI villa in Virgin Gorda

A fanciful pedestrian gate ushers you through Symbio's lushly-landscaped grounds and into the entry foyer, which is inlaid with a polished stone compass rose.

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Esprit

United States Virgin Islands, St. John

from $614 /night
up to 6 guests

Esprit

3 bedroom 3.5 bath USVI villa in St. John

Located in the Virgin Islands National Park on Bordeaux Mountain, St. John’s highest peak, sits Esprit, a luxurious Island retreat.

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Colibri Cottage

St. Lucia, Soufriere

from $610 /night
up to 12 guests

Colibri Cottage

6 bedroom 6 bath St. Lucia villa in Soufriere

Colibri Cottage is situated on Malgretoute Bay, a quiet haven for sailboats and yachts cruising the Caribbean.

Sky Blue

St. Martin, Sint Maarten

from $608 /night
up to 11 guests

Sky Blue

5 bedroom 5.5 bath St. Martin villa in Sint Maarten

Sky Blue is a luxurious, five-bedroom, ocean-view villa where you will see all the hues of the blue sky and ocean, located in the exclusive gated community of Dawn Beach Estates on St. Maarten.

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Tamarind Villa

St. Lucia, Gros Islet

from $605 /night
up to 14 guests

Tamarind Villa

7 bedroom 7 bath St. Lucia villa in Gros Islet

Tamarind Villa is a luxurious, hillside, seven-bedroom villa with magnificent views of the Caribbean and Atlantic, situated overlooking the golf course.

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Rockspray

Turks & Caicos, Providenciales

from $605 /night
up to 4 guests

Rockspray

2 bedroom 2 bath Turks & Caicos villa in Providenciales

Rock Spray, a private, refurbished, and delightfully unique Turks and Caicos vacation rental villa, is set on a peninsula surrounded on three sides by the stunning turquoise waters of Chalk Sound.

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Sugar Kube

Turks & Caicos, Providenciales

from $600 /night
up to 2 guests

Sugar Kube

1 bedroom 1.5 bath Turks & Caicos villa in Providenciales

Exquisitely designed and furnished, 'Sugar Kube' is a tranquil, one bedroom beach villa, just footsteps to spectacular Grace Bay Beach and Smith’s Reef—a snorkelers paradise.

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Fields of Ambrosia

St. Martin, Terres Basses

from $600 /night
up to 6 guests

Fields of Ambrosia

3 bedroom 3 bath St. Martin villa in Terres Basses

Welcome to Fields of Ambrosia, a stunning 3-bedroom luxury villa located in the exclusive area of Terres Basses on the island of St. Martin.

Glitter Bay 102 “49 Steps”

Barbados, Porters

from $600 /night
up to 4 guests

Glitter Bay 102 “49 Steps”

2 bedroom 2 bath Barbados villa in Porters

Glitter Bay 102 is a ground floor, two-bedroom unit with a fully air-conditioned, open-plan living area.

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Church Point #2

Barbados, Holetown

from $600 /night
up to 6 guests

Church Point #2

3 bedroom 3.5 bath Barbados villa in Holetown

Church Point Two is bright and breezy, and set among gloriously lush and tropical garden, and promises a truly carefree holiday experience.

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Brise de Mer

St. Lucia, Cap Estate

from $595 /night
up to 8 guests

Brise de Mer

4 bedroom 4.5 bath St. Lucia villa in Cap Estate

Let the stunning vista and ocean view entice and captivate you.

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Saline Reef

St. Lucia, Rodney Bay

from $595 /night
up to 6 guests

Saline Reef

3 bedroom 3.5 bath St. Lucia villa in Rodney Bay

The cliff-side Saline Reef in Cap Estate is a bright, modern villa with a beach house feel and stunning views.

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Joy Estate

St. Martin, Sint Maarten

from $590 /night
up to 10 guests

Joy Estate

5 bedroom 5.5 bath St. Martin villa in Sint Maarten

Situated at the top of Beethoven Drive, with one of the most impressive panoramic views, this 3 acre estate features massive 40 ft castle style rock walls with historic cannons.

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Jasmine

Anguilla, Meads Bay

from $577 /night
up to 4 guests

Jasmine

2 bedroom 2 bath Anguilla villa in Meads Bay

This two-bedroom villa is located in the northwestern part of Anguilla and offers luxury, relaxation, and an ocean view.

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Smuggler’s Nest

St. Lucia, Gros Islet

from $575 /night
up to 4 guests

Smuggler’s Nest

2 bedroom 2.5 bath St. Lucia villa in Gros Islet

This magnificent two-bedroom home is one of the finest in the whole Caribbean and was extensively described in one of the issues of Architectural Digest.

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Sol e Luna

St. Martin, St. Martin (French)

from $572 /night
up to 6 guests

Sol e Luna

3 bedroom 3.5 bath St. Martin villa in St. Martin (French)

Sol e Luna is a very pretty, French Creole style villa that blends Caribbean charm with a contemporary attitude.

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Ocean View

St. Martin, St. Martin (French)

from $572 /night
up to 6 guests

Ocean View

3 bedroom 3.5 bath St. Martin villa in St. Martin (French)

Ocean View has superb sunrise views over the ocean towards Tintamarre and St. Barth.

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Madras

St. Martin, Terres Basses

from $572 /night
up to 10 guests

Madras

5 bedroom 5 bath St. Martin villa in Terres Basses

Madras is a luxurious Caribbean villa situated in Terre-Basses, a private gated community area in French St Martin.

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Skyline at Tryall

Jamaica, Montego Bay

from $571 /night
up to 2 guests

Skyline at Tryall

1 bedroom 2 bath Jamaica villa in Montego Bay

Stella Marina is a very smart and well-presented one-bedroom villa with stunning ocean and golf course views.

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Luna

St. Martin, Sint Maarten

from $558 /night
up to 6 guests

Luna

3 bedroom 4.5 bath St. Martin villa in Sint Maarten

The all white villas make you feel as if you have landed in Greece and not St-Maarten.

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No Limit

St. Martin, St. Martin (French)

from $557 /night
up to 6 guests

No Limit

3 bedroom 4.5 bath St. Martin villa in St. Martin (French)

No Limit in St. Martin features beautiful sunsets and ocean views!

Anacapri Pool Deck Down Island

AnaCapri Estate

British Virgin Islands, Tortola

from $555 /night
up to 10 guests

AnaCapri Estate

4 bedroom 4.5 bath BVI villa in Tortola

'AnaCapri Estate' sits on a generous one-acre lot looking out over Tortola's breathtaking panorama of Guana Island, Great Camanoe, and over to The Dogs and Virgin Gorda.

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Mullins Bay 6 - Jasmine

Barbados, Mullins Bay

from $550 /night
up to 7 guests

Mullins Bay 6 - Jasmine

3 bedroom 3 bath Barbados villa in Mullins Bay

Jasmine at Mullins Bay is a three-bedroom luxury townhouse located within the exclusive Mullins Bay Development.

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Coconut Grove 2 at Royal Westmoreland

Barbados, Alleynes Bay

from $550 /night
up to 6 guests

Coconut Grove 2 at Royal Westmoreland

3 bedroom 3 bath Barbados villa in Alleynes Bay

Located on the prestigious Royal Westmoreland Golf Resort, Villa Grove is a recently renovated Three-Bedroom villa situated within the highly desirable Coconut Grove avenue.

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Villas on the Beach 101

Barbados, St. James

from $550 /night
up to 5 guests

Villas on the Beach 101

3 bedroom 3 bath Barbados villa in St. James

Villas on the Beach 101 is a ground floor, three-bedroom apartment with a large patio, offering spectacular sunset views over the sea.

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Moments at the Tryall Club

Jamaica, Montego Bay

from $550 /night
up to 4 guests

Moments at the Tryall Club

2 bedroom 2 bath Jamaica villa in Montego Bay

With over 2,500 square feet of living space, Moments is a two-bedroom villa suite that offers spectacular views and a spacious patio.

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Windsong - Bungalow Suites

Turks & Caicos, Providenciales

from $548 /night
up to 8 guests

Windsong - Bungalow Suites

3 bedroom 3 bath Turks & Caicos villa in Providenciales

With a coveted setting on the pristine white sands of Grace Bay Beach, Windsong Resort is the only four-star resort on Providenciales located directly on a snorkeling reef, which lies just 20 yards offshore.

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Windsong - Resort Suites

Turks & Caicos, Providenciales

from $548 /night
up to 3 guests

Windsong - Resort Suites

1 bedroom 1 bath Turks & Caicos villa in Providenciales

With a coveted setting on the pristine white sands of Grace Bay Beach, Windsong Resort is the only four-star resort on Providenciales located directly on a snorkeling reef, which lies just 20 yards offshore.

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Caza Lili

St. Barthélemy, Lorient

from $543 /night
up to 2 guests

Caza Lili

1 bedroom 1 bath St. Barthélemy villa in Lorient

Villa Caza Lili is ideally located a few steps away from Lorient beach, supermarkets, restaurants, and bakeries.

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Lune de Miel

St. Martin, St. Martin (French)

from $543 /night
up to 4 guests

Lune de Miel

2 bedroom 2 bath St. Martin villa in St. Martin (French)

The name of this two bedroom villa speaks for itself - in French it is truly a "Honeymoon."

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Jessamine

Barbados, Gibbes Beach

from $540 /night
up to 8 guests

Jessamine

4 bedroom 4 bath Barbados villa in Gibbes Beach

Situated on the West Coast of Barbados, Jessamine is set amidst lush tropical gardens approximately a 5-minute walk from the magnificent beach at Gibbs Bay, St. Peter.

Alfresco

British Virgin Islands, Tortola

from $540 /night
up to 6 guests

Alfresco

3 bedroom 3.5 bath BVI villa in Tortola

A wonderful luxury secluded property within a private hillside estate overlooking the beautiful Long Bay Beach.

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One Bedroom Oceanfront Suite at Bianca Sands

Turks & Caicos, Providenciales

from $531 /night
up to 2 guests

One Bedroom Oceanfront Suite at Bianca Sands

1 bedroom 1 bath Turks & Caicos villa in Providenciales

Located on a pristine 300-foot stretch of powder white sand on world-famous Grace Bay Beach, Bianca Sands on Grace Bay is rewriting the rules on island luxury.

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473 Grenada Boutique Resort - Garden Villa

Grenada, New Westerhall Point

from $530 /night
up to 4 guests

473 Grenada Boutique Resort - Garden Villa

2 bedroom 2 bath Grenada villa in New Westerhall Point

At the water’s edge flanked between two secluded sandy beaches, 473 Grenada Boutique Resort opened in 2018 as a hideaway in the prestigious Fort Jeudy south coast region, on Grenada.

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Secret Garden

Barbados, St. James

from $530 /night
up to 6 guests

Secret Garden

3 bedroom 3 bath Barbados villa in St. James

Secret Garden at Merlin Bay is a lovely three bedroom fully air-conditioned villa with a private plunge pool set on two floors.

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Linga-Awile Cottage on the Beach

Jamaica, Discovery Bay

from $519 /night
up to 6 guests

Linga-Awile Cottage on the Beach

3 bedroom 4 bath Jamaica villa in Discovery Bay

This 3-bedroom casual cottage shares a delightful waterfront site with its neighboring Villa, on the clear waters of Discovery Bay. Linga-Awile sits on a lovely, long, large lawn. Beyond the lawn and swimming pool is its sugary white sand beach with two thatched roof umbrellas for shade.

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Kessi

St. Lucia, Gros Islet

from $510 /night
up to 6 guests

Kessi

3 bedroom 3 bath St. Lucia villa in Gros Islet

This spacious villa is located on South Hill, in Cap Estate with views of the Caribbean Sea and the Atlantic Ocean.

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La Nina

St. Martin, St. Martin (French)

from $500 /night
up to 4 guests

La Nina

2 bedroom 2.5 bath St. Martin villa in St. Martin (French)

This charming Creole style villa is a peaceful oasis set in a lush and colorful tropical garden.

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Summertime at Silver Sands

Jamaica, Montego Bay

from $500 /night
up to 8 guests

Summertime at Silver Sands

4 bedroom 4 bath Jamaica villa in Montego Bay

Summertime at Silver Sands has a wonderful beach vibe, it benefits from cool sea breezes and is a relaxed and unfussy villa located on the renowned Silver Sands Beach Club, a collection of privately owned villas all overlooking the Caribbean sea.

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Sugar Cane Ridge 1 at Royal Westmoreland

Barbados, Alleynes Bay

from $500 /night
up to 6 guests

Sugar Cane Ridge 1 at Royal Westmoreland

3 bedroom 3 bath Barbados villa in Alleynes Bay

Sugar Cane Ridge 1 is a well-appointed, modern Caribbean villa, nestled in the exclusive Royal Westmoreland Golf Resort in Barbados, overlooking the beautifully landscaped short-game and putting areas of the Resort.

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Sol Y Mar

St. Martin, Sint Maarten

from $500 /night
up to 8 guests

Sol Y Mar

3 bedroom 3 bath St. Martin villa in Sint Maarten

Sol Y Mar, a charming second-level private penthouse villa, nestled between a vibrant collection of favorite eateries, bars, branch style bakeries and the lapping turquoise waters of Simpson Bay – the heartbeat of the Dutch side.

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Sea Haven on Discovery Bay

Jamaica, Discovery Bay

from $500 /night
up to 8 guests

Sea Haven on Discovery Bay

4 bedroom 4 bath Jamaica villa in Discovery Bay

Located on a private waterfront acre, Sea Haven is a traditional West Indian cottage dressed in charming periwinkle blue and sitting directly on the edge of beautiful Discovery Bay.

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Mullins View 14

Barbados, Mullins Bay

from $500 /night
up to 8 guests

Mullins View 14

4 bedroom 4 bath Barbados villa in Mullins Bay

This spacious, four-bedroom villa is impeccably furnished, has a comfortable living area and a large, covered terrace with both dining and living areas.

Caneel Trailside Cottage

United States Virgin Islands, St. John

from $500 /night
up to 4 guests

Caneel Trailside Cottage

2 bedroom 2 bath USVI villa in St. John

Caneel Trailside Cottage sits one mile outside Cruz Bay, high up on the ridge in the saddle between Caneel Hill and Margaret Hill, adjacent to the Virgin Islands National Park.

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Royal Villa 19 at Royal Westmoreland

Barbados, St. James

from $500 /night
up to 6 guests

Royal Villa 19 at Royal Westmoreland

3 bedroom 3.5 bath Barbados villa in St. James

The perfect villa for a family vacation located within the Royal Apartments in the prestigious Royal Westmoreland, Barbados.

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Falaise des Oiseaux

St. Martin, St. Martin (French)

from $500 /night
up to 6 guests

Falaise des Oiseaux

3 bedroom 3 bath St. Martin villa in St. Martin (French)

From its dramatic cliff-top location, on the northern coastline of French St. Martin in Terres Basses, villa Falaise des Oiseaux enjoys sublime water views across the ocean to the neighboring island of Anguilla on the distant horizon.

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Etoile at the Tryall Club

Jamaica, Montego Bay

from $493 /night
up to 2 guests

Etoile at the Tryall Club

1 bedroom 1 bath Jamaica villa in Montego Bay

A beautifully presented one-bedroom villa with outstanding ocean views looking east towards Montego Bay.

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Blue Sailing

St. Martin, St. Martin (French)

from $485 /night
up to 6 guests

Blue Sailing

3 bedroom 3 bath St. Martin villa in St. Martin (French)

Blue Sailing is a cozy three bedroom villa located in the private Happy Bay Estate, St Martin.

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Mirador at the Tryall Club

Jamaica, Montego Bay

from $482 /night
up to 2 guests

Mirador at the Tryall Club

1 bedroom 2 bath Jamaica villa in Montego Bay

Mirador is a stylish one-bedroom apartment at the posh Tryall Club. Its prize location provides both proximity to the elegant Tryall Club Great House and a breathtaking view over the deep blue Caribbean Sea and the manicured championship golf course.

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